April 19, 2022

36: My Journey in Leaving Corporate

This is a personal and emotional episode. In the months leading up to quitting corporate in March 2022, I recorded my thoughts and feelings. This episode is a compilation of those recordings — a personal journal, if you will.

I discuss why I needed to make the leap, including the strategy and mindset that made it possible. I hope it helps you identify the “leaps” worth making in your life.

Ready to take ownership of your career and life? I’ve got something next-level for you: the Uncaged Academy.



01:35 90 DAYS out from resignation

05:58 60 DAYS out from resignation

09:14 People stuck in their Matrix

11:20 Leaving corporate as a forcing function for growth

13:55 Anticipation (visualization) of Freedom Day

14:38 30 DAYS out from resignation

15:48 Readying to lose my “guaranteed” paycheck

19:01 Feeling “alive” as I’ve cultivated my passion

21:20 7 DAYS out from resignation

24:16 Default Path vs. Pathless Path (Paul Millerd)

26:33 Resignation (Freedom) day

28:02 I resigned from corporate!



1. After life fell apart for me, I took control of my corporate situation over recent years and found ways to operate on my own terms.


2. Soon, I was helping others do the same, and I discovered the seeds of a new entrepreneurial business.


3. COVID allowed me to experiment and lay the groundwork for a post-corporate life. 


4. Personally, I eventually felt it wasn’t risky to leave corporate. It was riskier to stay — living a “small” life,  being undiversified, denying my burning inner purpose.


5. I realized I could model out my net worth, free time, etc. in corporate for decades ahead. That “cap” scared me. I’d rather have uncapped potential.


6. Imposterism (imposter syndrome) took hold early on as I contemplated entrepreneurial life. I had to train my mind to welcome the shift as a worthy fear.


7. Leaving the corporate “safety net” became a forcing function for me to become who I’m capable of being.


8. I had to get comfortable with not having a rigid plan or “ideal results” before taking the leap.


9. I worked with my coach to execute a strategic, well-planned exit from corporate. I wasn’t going to leave my family (including wife and 4 kids) in a tough situation.


10. With massive moves in life (e.g., buying a house, having a kid, starting a business), the timing just has to be “good enough.” It’ll never be perfect. Trust yourself. 



Join the Uncaged Academy (cohort-based course)

Subscribe to the Wednesday Wisdom newsletter

Connect w/ Matt on LinkedIn

Follow on Twitter @MatthewRDoan

Check the show on YouTube

Related episodes: Self-Reliance (#17), Imposter Syndrome (#30)